So you have your Eccentric Mentor and with his backing you're facing off against the nefarious machinations of the local Evil Sorcerer, when suddenly you learn a shocking truth — in their youth, rather than being bitter enemies, these guys were best friends!
This trope occurs whenever a good aligned character (sometimes The Hero, but more commonly The Obi-Wan, the Eccentric Mentor, the Supporting Leader, or the Big Good) is revealed to have had a history as friend, ally, mentor, or even student with a major villain (commonly the Big Bad, but sometimes The Dragon or another high-ranking Evil Minion). Usually the friendship fell through simply because the future villain went power mad and the other character didn't want any more to do with it, but more complex and unusual variations exist. Sometimes it will be known all along, but sometimes it will be the subject of a dramatic reveal that can lead The Hero and the audience to reevaluate what they know about both characters.
As the top of the page indicates, tends to happen a disproportionate amount of the time with the resident Wise Old Wizard and the Evil Sorcerer. Compare and contrast Big Bad Friend, where the revelation occurs during the story and the "Bad" character was evil all along (or at least had been for a while) and would rather remain friends despite this. Usually, either the evil character will be a Fallen Hero or the good one will be The Atoner (or both, if both started out more morally grey). The evil character will most likely be an Evil Counterpart and/or Shadow Archetype for the good one, and may also be their Arch-Enemy. If traces of the past friendship still exist, they might be Friendly Enemies or even have Foe Yay. Compare and contrast Rival Turned Evil, for where the friendship broke up over personal rivalry before one of the characters turned evil (though certain examples will overlap, not all will). A less extreme version of the falling-out is We Used to Be Friends.
Note that this is about friends who turned evil in the Backstory and are either introduced or established in their first appearance as villains. If the friend turns evil over the course of the work, see Face-Heel Turn.
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In Naruto, Jiraiya, Tsunade and Orochimaru were once on the same squad. Jiraiya was Orochimaru's closest friend, before Orochimaru abandoned the Leaf Village. Jiraiya chased him down and tried to talk him out of it, but Orochimaru laughed in his face.
Kazuma of the 12 Guardian Ninjas filler arc was one to Asuma, as they served together in the Guardian Ninjas until Kazuma betrayed the group with five of his comrades to pursue their extremist agenda of making the daimyo the sole authority of the nation.
Tobi has been revealed to be Obito Uchiha, Kakashi's best friend and role model. The pain of this revelation left Kakashi reeling in shock long enough to nearly be killed.
This hearkens back to his own relationship with Itachi. Sasuke absolutely adored his older brother, only for him to murder their entire clan. His conflicting love for his brother and hate for what he had done were eventually used by Tobi to manipulate him.
Madara Uchiha and Hashirama Senju were good friends despite the intense rivalry between their clans, enough that after years of war they were able to work together to found Konoha. Despite this, the mistrust of Hashirama's brother eventually convinced Madara to turn his back on Konoha and become the Big Bad.
Regius for Zest in Magical Girl Lyrical Nanoha StrikerS. The two used to be friends while serving together in the bureau, and wanted to ensure that the Bureau's ground forces were able to deal with criminals and other threats. Over time, Regius lost sight of his ideals as he fell under the sway of the High Council, and eventually Zest and nearly all his team were killed on a raid on a Combat Cyborg facility. Zest, after being cloned, sought out Regius for answers on why he changed, but Due killed Regius before he could give any.
In Fushigi Yugi, Miaka and Yui are both best friends until the two are pitted against each other. The odd thing about this particular example is that Yui is deceived into thinking Miaka is the one who turned against her, and that she, not Yui, is the one who is turning evil.
In Suite Pretty Cure ♪, Siren and Hummy used to be the best of friends until Hummy took Siren's title as singer of the annual "Melody of Happiness", causing the latter to defect to the villains' side. They almost made up early in the series before Mephistoforcefully won Siren's loyalty back. However, they do get a proper reconcilliation about nine episodes later, leading to Siren joining the team as Cure Beat.
Who else but Guts and Griffith of Berserk? The two men had a bond bordering on brotherhood (or if you're that way inclined, more than that), only for Griffith to turn his back on him and everyone else he led during the events of the Eclipse, which would destroy this bond forever and leave Guts with an undying hatred for Griffith.
In AKIRA, Tetsuo is this to Kaneda. Both have been friends since their first meeting in an orphanage.
Shin used to be Kenshiro's best friend in Fist of the North Star up until he was manipulated by Kenshiro's evil brother Jagi into turning against him and taking Yuria, who both Kenshiro and Shin loved, for himself.
In Rave Master, Gale Raregroove, aka King the leader of Demon Card, and Gale Glory, Haru's father, used to be the best of friends. A huge helping of tragedy and poor decisions made them bitter enemies. The worst part is that it's implied near the end of the series that this was partly due to fate constantly screwing over the Raregroove bloodline.
Wolverine and Sabretooth. As of Origin II, it's revealed that the two met when Victor was an animal tracker. Creed tracked down a feral Logan for a circus, and his sister Clara was Logan's handler. First X-Men actually shows us why the two went their separate ways. After forming a group of mutant rebels to fight the government, Victor wants to take off with his love interest and leave the fighting to someone else. However, Wolverine, by that point, had already convinced everyone that what they were doing was necessary, so she stayed. She is killed in the final conflict and Creed blames Logan.
Black Mask and Hush were both Bruce Wayne's childhood friends, having turned into supervillains in their adult lives.
Apparently Megatron and Optimus were this in the IDW continuity and in the Movie prequel comics and Marvel UK annuals as well.
On Tatooine, Luke Skywalker only had two friends who shared his desire to go offworld, and both, being older than him, joined the Imperial military before A New Hope. Biggs Darklighter became a pilot, defected to the Rebellion, and died at Yavin. Luke's other friend, Janek "Tank" Sunber, was shown in the comics; he washed out of pilot training and became an infantry officer. Of course, he came into conflict with Luke.
In the New 52, Nightwing's newest foe Saiko is former friend and fellow former member of Haly's circus Raymond. Raymond was taken by the Court of Owls and put through Training from Hell to become a Talon, only to be washed out and left for dead with his eyes pecked out by birds. Saiko hates Dick Grayson because the Court only took Raymond because they couldn't get Dick, their original candidate, after Bruce Wayne adopted him in the wake of the Flying Graysons' deaths.
Reed Richards and Doctor Doom were college students who could only find intellectual debate and stimulation from each other, until Reed pointed out a mistake in Victor's schematics which was part of his last step in his Start of Darkness.
In The Flash, there's Hunter Zolomon, formerly a close Friend on the Force to Wally West, before Gorilla Grodd broke his back and set the stage for him to become Zoom.
Darth Vader and Obi-Wan from Star Wars are a double-hitter, as Vader (as Anakin Skywalker) was both Obi-Wan's student and his closest friend.
Count Dooku was also once a respected Jedi Master who got on well with his former teacher Yoda and peer Mace Windu. In this case the revelation, especially to the characters, was the fact that he'd turned evil rather than that he had been someone's friend.
Toy Story 3 Inverts this: Chuckles the Clown was friends with Lotso, who is the Big Bad. Witnessing Lotso become a monster resulted in him becoming bitter and cynical.
Popular folklore has Billy the Kid and Pat Garret as an example of this, although their friendship was never actually documented.
Several times in Harry Potter — Albus Dumbledore and Gellert Grindelwald were best friends (and a bit more, at least on Albus's end). Later on, Tom Riddle, the future Lord Voldemort, was Dumbledore's student, and at least one of the Sorting Hat's songs implies that Godric Gryffindor and Salazar Slytherin were once good friends as well.
Subverted with Sirius Black, who looks like the evil part of this in comparison to Harry's dad, but is revealed to have been framed. Played straight with Peter Pettigrew, another former friend who was guilty and did the framing.
As well as Lily Evans and Severus Snape, until the latter's Heel-Face Turn.
Gandalf and Saruman from The Lord of the Rings have elements of this, though their relationship doesn't shatter until early in the present storyline (though the books at least show that it had been fraying for a while before that because of Saruman's jealousy).
They had never been exactly good buddies; according to the Appendix Saruman had been jealous of Gandalf almost as soon as they stepped off the ship in the Gray Havens, but they had had mutual respect and a common purpose.
Warbreaker has Vasher and Denth as an interesting variation because the friendship ended violently over something Vasher, the good guy of the two did. They were originally part of the same group of famous magic-users, and Vasher killed Denth's sister, another member, fearing that her knowledge of how to create Artifacts of Doom would spread. Denth went on a Roaring Rampage of Revenge to avenge her, gradually descending into evil in the process.
Though calling them "friends" would be a stretch (he was never a particularly nice guy), Zedar from The Belgariad was once a Disciple of Aldur along with the Eccentric Mentor Belgarath, and the two worked closely together and respected each other. Then TorakMind Raped Zedar into becoming The Dragon, and it went rapidly downhill from there.
From The Elenium, comparatively rare example of the main hero having a prominent villain as one of these- Martel and Sparhawk were good friends who went through Magic Knight training together, until Martel got caught practicing Black Magic and was expelled from the order. Though now enemies, they're still very polite to each other and respect each other's abilities, and conduct their final duel in a most gentlemanly manner.
From The Tamuli, Sephrenia and Zalasta had been friends from childhood, and Styric lifespans are very long. It didn't end well. Unfortunately for everyone, Zalasta was driven by a very extreme case of Love Makes You Evil.
In Memoirs of a Geisha, Sayuri and Pumpkin, who started out as friends, but once Mother adopted Sayuri instead of Pumpkin and she became a more popular geisha than Pumpkin, they became rivals (at least in Pumpkin's mind).
The Doctor and the Master, from Doctor Who. They're still sort of Friendly Enemies, but when they were schoolkids together, they weren't enemies at all, and the Doctor has some serious angst about this.
Burn Notice has Michael Westen's former partner-in-spying Larry Sizemore, who becomes a Psycho for Hire after he faked his death in Serbia. He shows up in Miami running a sort of freelance assassination business; he shows up in a few episodes, during which he forces Michael into Enemy Mine situations.
On Justified US Marshal Raylan Givens and local criminal Boyd Crowder grew up in the same community and then 'dug coal together' in the local coal mine. The show starts when Raylan is forced to return to Kentucky and has to confront Boyd who in the meantime became the leader of a Neo-Nazi gang of bank robbers.
House of Anubis. For Sarah Frobisher-Smythe, both Victor Rodenmaar and Rufus Zeno fit this trope. Victor and Rufus, being the two major villains of season 1 and both major again in season 2, as well as both antagonizing Sarah for a secret she doesn't have, were both once Sarah's childhood friends and eventually business partners, until they both became corrupted with power and greed and turned on her, and each other as well.
Regina to Snow White on Once Upon a Time. It's played for a fair amount of tragedy too. There are a number of scenes devoted to showing how Regina changed from a kind, caring young girl to a vicious Evil Sorceress.
Many tellings of the Satan story will have pre-Fall Lucifer as God's favorite angel. In some, he was Archangel Micheal's closest friend.
Delia Ketchum used to date Giovanni in the Pokémon Live! musical. In an original draft of the show, Giovanni was Ash's father.
Wicked has an interesting take on this (and this is true for the novel as well): although neither Elphaba nor Glinda is truly a villain in the novel at hand, its entire premise is that it functions as backstory to the original The Wizard of Oz. If one were to take Wicked as behind-the-scenes canon for Wizard, Elphaba's and Glinda's relationship — as friends in the former and on opposite sides of the conflict in the latter — would certainly qualify.
In LEGO's Legends Of Chima line, the main protagonist Laval of the lion tribe used to be friends with Cragger of the crocodile tribe before the latter got a taste of Chi and inadvertantly started the war that the story revolves around. Similarly, he was friends with Worriz of the wolf tribe before they allied themselves with the crocs under Cragger's leadership.
Phoenix Wright and Miles Edgeworth in Phoenix Wright: Ace Attorney. Miles and Phoenix were good friends in elementary, until the DL-6 incident which killed Miles' father and traumatized Miles. Then to put the icing on the cake, Manfred von Karma adopted Miles and raised him in the corrupt ways of the Von Karma family. The two friends meet again in the courtroom; Phoenix on the defense bench and Miles on the prosecutor's bench. Then, as the series goes on, they become friends again, or at least win back each other's respect, as Edgeworth gains Character Development.
Case 1-5 has this with Lana Skye and her old co-workers, Angel Starr and Jake Marshall. They all worked together to catch the serial killer Joe Darke, but then Lana grew cold and distant and rumors began to fly that she was using less-than-legitimate methods to catch criminals. As it turns out, she was being blackmailed. This is also implied to be the case between the Judge and Damon Gant.
Subverted in Dual Destinies, with Athena and Simon. While they had once been friends when Simon worked with Athena's mother, and apparently ended up killing her, it's revealed that not only was Simon not the murderer, Athena never believed he was and has spent her life trying to prove it.
Dr. Light and Dr. Wily had this relationship in Mega Man.
Revan and Malak in Knights of the Old Republic. Inverted in that it's common knowledge that they used to be friends; the twist is that Revan is still alive and back with the Jedi. During their final confrontation, a redeemed Revan can even apologise for leading their friend down the path to the Dark Side, but note that it was ultimately Malak's decision to continue down that path.
The lead signature characters of City of Heroes and City of Villains, Statesman and Lord Recluse, respectively, were best friends before Recluse joined Arachnos.
Pigma Dengar was on the original Star Fox team before his betrayal.
In Transformers: War For Cybertron it's taken it Up to Eleven, with Optimus being swayed to help start Megatron's rebellion, and even successfully lobbying for the Council to grant the rebels an audience... where Optimus argued his understanding of Megatron's cause so well, the Council agreed and named Optimus the next Prime. Megatron saw this as a betrayal, and started the civil war, anyway. Nice Job Breaking It, Hero, indeed.
"Arthur," in the Sega Genesis version of Ghostbusters, to the Weapons Shop owner.
"Did Arthur die? Once he was my friend. After he found the stone tablet he changed, but a long time ago he was a good man. To restore his good name, I'll repay you for your costs."
Persona 3's backstory has strong shades of this. Nearly everyone in the know about the Dark Hour (outside of about half your party) used to work together for the Kirijo Group's "Ergo Division" that researched Personas and Shadows, or were involved in their initial researches. Not all of them may have been friends, as such (Strega has a very understandable grudge against Kirijo), but there are a lot of old professional relationships gone sour due to Mitsuru's grandfather's megalomania and the disasters it caused (and continues to cause).
In one story in the Whateley Universe, Phase muses on how a lot of the time, villains started off as the hero's best friend, and wonders if one day he'll end up enemies with his friends Mal and Jadis, who are the children of supervillains (Mal wants to be a villain and Jadis hasn't said whether she wants to be a hero or not, though the answer is probably yes).
Anyone who has played Mortal Kombat will know of the rivalry between Hanzo Hasashi (Scorpion) and Bi-Han (Sub-Zero), stemming from Evil Sorcerer Quan Chi disguising himself as Bi-Han and murdering Hanzo's entire clan and family. However, in the second season of Mortal Kombat Legacy, we find out that they were childhood friends, despite their parents forbidding them from playing together due to the rivalry between their ninja clans. In fact, after they become the leaders of their respective clans, they declare peace, and Bi-Han is even willing to keep the peace after Hanzo is forced to kill Bi-Han's brother while protecting his family. Shortly after that, Hanzo and the the entire Shirai Ryu clan are slaughtered, apparently by Bi-Han and his Lin Kuei ninja. When Bi-Han finds out, he is ready to execute his lieutenants on the spot for this until he finds out that they weren't responsible. After Hanzo becomes the undead Scorpion and joins the Mortal Kombat tournament on the side of the Netherrealm, he faces Bi-Han in combat. Bi-Han's attempts to reach his childhood friend fall on deaf ears, and Hanzo ends up killing him in a gruesome way.
Fire Lord Sozin, the guy who started the War and the tradition of Fire Lords being Evil Overlords, was once best friends with Avatar Roku on Avatar: The Last Airbender , though in a variation both characters are long dead by the time the viewer learns the details of their history.
Vlad Masters from Danny Phantom was Danny's parents' best friend in college, until a botched experiment dreamed up by Danny's dad Jack (temporarily) disfigured him (and gave him superpowers, but he didn't find that out until later). Vlad is now dedicated towards three goals- killing Jack, convincing Maddie (Danny's mom) to fall in love with him, and making Danny his apprentice. Ironically, Jack is the only one completely oblivious to all this.
In an episode where Danny tries to stop the accident that turned Vlad into a ghost, it was shown that Vlad was already jealous of Jack and his relationship with Maddie, and implies he would have still sought out Maddie even without ghost powers.
The Batman gives us Ethan Bennett, both a high-school friend of Bruce Wayne's and one of the only cops willing to give Batman a chance. Naturally, he's accidentally turned into Clayface in the Season 1 finale. He eventually becomes a good guy again after spending a while in the Heel-Face Revolving Door.
Terry McGinnis also received this treatment when his old friend fell back into crime and became Big Time in Batman Beyond.
In season 3 of Xiaolin Showdown, we discover that Chase Young is this to Master Monk Guan from before Chase was turned Heylin by Hannibal Bean.Technically, he is this to Grand Master Dashi as well, except that Dashi is assumedly dead in the present.
Similar to Cy-Kill and Leader-1 below Optimus and Megatron used to be close as brothers in Transformers Prime.
Cy-Kill used to be Leader-1's closest comrade in Challenge Of The Go Bots. He defected out of jealousy over Leader-1's successes.
In M.A.S.K., Matt Trakker and Miles Mayhem were friends who formed MASK together, before Mayhem stole some of the masks and used them to set up VENOM.
Wheeljack in Transformers Armada was friends with Hot Shot before Hot Shot betrays him...or so Wheeljack thinks. Turns out Hot Shot tried to go back and save him, but failed.
In BIONICLE's 2004 line, Lhikan and Nidhiki use to be close friends as Toa, but Nidhiki betrayed his fellow Toa to the Dark Hunters. When his plan failed, Nidhiki was transformed into an insectoid monster.
In the Captain N: The Game Master episode "The Most Dangerous Game Master" Dr. Wily builds an android rival based on Kevin's memories of a school bully. Later we find out Kevin and the bully used to be friends, and since the bully was created from Kevin's memories he still retains his good traits and Kevin is able to befriend him again.
General Modula, the Big Bad of Sym-Bionic Titan, was this to the King of Galaluna prior to the series, also as seen in a flashback in "Shadows of Youth."
In SheZow, Tara was the sidekick to Guy's aunt Agnes, the previous SheZow, but eventually faded into obscurity. When she first appears she wants to bury the hatchet, but Guy not knowing who she is causes her to snap and challenge him to a duel instead, namely "GLAMAGEDDON-GEDDON-GEDDON!"
In El Tigre: The Adventures of Manny Rivera, White Pantera's ex-sidekick, the Titanium Titan, turns evil after White Pantera's son Manny was born and resents him for having his partner's attention. He becomes obsessed with getting rid of El Tigre so he can have White Pantera to himself again.